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Modified Ozonolytic Synthesis of 4Z-Nonen-1-ol, an Intermediate for the Synthesis of Sex Pheromones of Cotton Bollworm and Cabbage Moth, from the Cyclic Butadiene-Isoprene Codimer

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

An improved procedure for preparing 4Z-nonen-1-ol, a key intermediate in the synthesis of sex pheromones of cabbage moth and cotton bollworm, from the cyclic butadiene-isoprene dimer (1-methyl-1Z,5Z-cyclooctadiene) was developed. In this procedure, the peroxide product of regioselective partial ozonolysis (0.9 equiv of O3) of the codimer across the trisubstituted double bond is converted in one step to 9-hydroxy-5Z-nonen-2-one with NaBH(OAc)3, the reagent that does not affect the keto groups present in the structure or formed in the process.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, Bashkortostan, 450054, Russia

    G. Yu. Ishmuratov, Yu. V. Myasoedova, L. R. Garifullina, E. R. Nurieva & N. M. Ishmuratova

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  1. G. Yu. Ishmuratov
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  2. Yu. V. Myasoedova
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  3. L. R. Garifullina
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  4. E. R. Nurieva
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  5. N. M. Ishmuratova
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Correspondence to G. Yu. Ishmuratov.

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Ishmuratov, G.Y., Myasoedova, Y.V., Garifullina, L.R. et al. Modified Ozonolytic Synthesis of 4Z-Nonen-1-ol, an Intermediate for the Synthesis of Sex Pheromones of Cotton Bollworm and Cabbage Moth, from the Cyclic Butadiene-Isoprene Codimer. Russ J Appl Chem 92, 244–247 (2019). https://doi.org/10.1134/S1070427219020113

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  • DOI: https://doi.org/10.1134/S1070427219020113

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